ES2202796T3 - Derivados de acidos arilsulfonilaminohidroxamicos. - Google Patents

Derivados de acidos arilsulfonilaminohidroxamicos.

Info

Publication number: ES2202796T3
Authority: ES; Spain
Prior art keywords: aryl; heteroaryl; alkyl; aril; aryloxy
Prior art date: 1997-02-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES98900021T

Other languages

English (en)

Spanish (es)

Inventor

Ralph Pelton Robinson, Jr.

Kim Francis Mcclure

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Products Inc

Original Assignee

Pfizer Products Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-02-03

Filing date

1998-01-12

Publication date

2004-04-01

1998-01-12 Application filed by Pfizer Products Inc filed Critical Pfizer Products Inc

2004-04-01 Application granted granted Critical

2004-04-01 Publication of ES2202796T3 publication Critical patent/ES2202796T3/es

2018-01-12 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
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150000003460 sulfonic acids Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical group CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
DRDCQJADRSJFFD-UHFFFAOYSA-N tris-hydroxymethyl-methyl-ammonium Chemical compound OC[N+](C)(CO)CO DRDCQJADRSJFFD-UHFFFAOYSA-N 0.000 description 1
239000002753 trypsin inhibitor Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Virology (AREA)
Pain & Pain Management (AREA)
Orthopedic Medicine & Surgery (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Oncology (AREA)
Dermatology (AREA)
Immunology (AREA)
Communicable Diseases (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Plural Heterocyclic Compounds (AREA)

ES98900021T 1997-02-03 1998-01-12 Derivados de acidos arilsulfonilaminohidroxamicos. Expired - Lifetime ES2202796T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US3685797P	1997-02-03	1997-02-03
US36857P		1997-02-03

Publications (1)

Publication Number	Publication Date
ES2202796T3 true ES2202796T3 (es)	2004-04-01

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ID=21891041

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Application Number	Title	Priority Date	Filing Date
ES98900021T Expired - Lifetime ES2202796T3 (es)	1997-02-03	1998-01-12	Derivados de acidos arilsulfonilaminohidroxamicos.

Country Status (42)

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US (1)	US6303636B1 (uk)
EP (1)	EP0977733B1 (uk)
JP (1)	JP3765584B2 (uk)
KR (1)	KR100317146B1 (uk)
CN (1)	CN1113862C (uk)
AP (1)	AP826A (uk)
AR (1)	AR011101A1 (uk)
AT (1)	ATE248812T1 (uk)
AU (1)	AU721748B2 (uk)
BG (1)	BG64308B1 (uk)
BR (1)	BR9807815A (uk)
CA (1)	CA2279276C (uk)
CO (1)	CO4920234A1 (uk)
DE (1)	DE69817801T2 (uk)
DK (1)	DK0977733T3 (uk)
DZ (1)	DZ2410A1 (uk)
EA (1)	EA002594B1 (uk)
ES (1)	ES2202796T3 (uk)
GT (1)	GT199800025A (uk)
HN (1)	HN1998000011A (uk)
HR (1)	HRP980058B1 (uk)
HU (1)	HUP0000852A2 (uk)
ID (1)	ID22799A (uk)
IL (2)	IL131042A (uk)
IS (1)	IS1950B (uk)
MA (1)	MA26471A1 (uk)
MY (1)	MY121754A (uk)
NO (1)	NO313631B1 (uk)
NZ (1)	NZ336840A (uk)
OA (1)	OA11081A (uk)
PA (1)	PA8445801A1 (uk)
PE (1)	PE57799A1 (uk)
PL (1)	PL335027A1 (uk)
PT (1)	PT977733E (uk)
SK (1)	SK283963B6 (uk)
TN (1)	TNSN98019A1 (uk)
TR (1)	TR199901849T2 (uk)
TW (1)	TW509668B (uk)
UA (1)	UA63935C2 (uk)
UY (1)	UY24866A1 (uk)
WO (1)	WO1998033768A1 (uk)
ZA (1)	ZA98823B (uk)

Families Citing this family (313)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1265647A (zh)	1997-07-31	2000-09-06	普罗克特和甘保尔公司	无环金属蛋白酶抑制剂
PA8469301A1 (es)	1998-04-10	2000-09-29	Pfizer Prod Inc	Procedimientos para la preparacion de acidos hidroxamicos.
GT199900044A (es) *	1998-04-10	2000-09-14		Procedimientos para preparar haluros de fenoxifenilsulfonilo.
PA8469601A1 (es)	1998-04-10	2000-09-29	Pfizer Prod Inc	Procedimiento para alquilar sulfonamidas impedidas estericamente
UA59453C2 (uk) *	1998-08-12	2003-09-15	Пфайзер Продактс Інк.	Похідні гідроксипіпеколат гідроксамової кислоти як інгібітори матричних металопротеїназ
US6858598B1 (en)	1998-12-23	2005-02-22	G. D. Searle & Co.	Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia
EP1147085B1 (en)	1999-01-27	2005-11-16	Wyeth Holdings Corporation	Alkynyl containing hydroxamic acid derivatives, their preparation and their use as matrix metalloproteinase (mmp) inhibitors / tnf-alpha converting enzyme (tace) inhibitors
US6762178B2 (en)	1999-01-27	2004-07-13	Wyeth Holdings Corporation	Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid TACE inhibitors
US6225311B1 (en)	1999-01-27	2001-05-01	American Cyanamid Company	Acetylenic α-amino acid-based sulfonamide hydroxamic acid tace inhibitors
US6313123B1 (en)	1999-01-27	2001-11-06	American Cyanamid Company	Acetylenic sulfonamide thiol tace inhibitors
US6340691B1 (en)	1999-01-27	2002-01-22	American Cyanamid Company	Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase and tace inhibitors
US6277885B1 (en)	1999-01-27	2001-08-21	American Cyanamid Company	Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid TACE inhibitors
US6200996B1 (en)	1999-01-27	2001-03-13	American Cyanamid Company	Heteroaryl acetylenic sulfonamide and phosphinic acid amide hydroxamic acid tace inhibitors
US6753337B2 (en)	1999-01-27	2004-06-22	Wyeth Holdings Corporation	Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase/tace inhibitors
US6326516B1 (en)	1999-01-27	2001-12-04	American Cyanamid Company	Acetylenic β-sulfonamido and phosphinic acid amide hydroxamic acid TACE inhibitors
US6946473B2 (en)	1999-01-27	2005-09-20	Wyeth Holdings Corporation	Preparation and use of acetylenic ortho-sulfonamido and phosphinic acid amido bicyclic heteroaryl hydroxamic acids as TACE inhibitors
CA2366954A1 (en)	1999-03-03	2000-09-08	The Procter & Gamble Company	Dihetero-substituted metalloprotease inhibitors
CZ20013176A3 (cs)	1999-03-03	2002-04-17	The Procter & Gamble Company	Sloučenina vytvářející inhibitor metaloproteinasy, farmaceutický prostředek, způsob přípravy léčiva a léčivo
WO2000058280A1 (fr) *	1999-03-26	2000-10-05	Shionogi & Co., Ltd.	Derives de sulfonamide carbocyclique
EP1041072B1 (en)	1999-03-31	2003-07-16	Pfizer Products Inc.	Dioxocyclopentyl hydroxamic acids
ES2208315T3 (es)	1999-05-28	2004-06-16	Pfizer Products Inc.	Hidroxiamidas de acidos 3-(arilsulfonamido)-tetrahidropiran-3-carboxilicos.
HN2000000052A (es) *	1999-05-28	2001-02-02	Pfizer Prod Inc	Hidroxiamidas de acidos 3- (arilsulfonilamino)- tetrahidrofuran-3-carboxilicos.
GB9918684D0 (en) *	1999-08-09	1999-10-13	Novartis Ag	Organic compounds
IL138686A0 (en) *	1999-10-01	2001-10-31	Pfizer Prod Inc	α- SULFONYLAMINO HYDROXAMIC ACID INHIBITORS OF MATRIX METALLOPROTEINASES FOR THE TREATMENT OF PERIPHERAL OR CENTRAL NERVOUS SYSTEM DISORDERS
UA74803C2 (uk)	1999-11-11	2006-02-15	Осі Фармасьютікалз, Інк.	Стійкий поліморф гідрохлориду n-(3-етинілфеніл)-6,7-біс(2-метоксіетокси)-4-хіназолінаміну, спосіб його одержання (варіанти) та фармацевтичне застосування
US7141607B1 (en)	2000-03-10	2006-11-28	Insite Vision Incorporated	Methods and compositions for treating and inhibiting retinal neovascularization
JP2003528082A (ja)	2000-03-21	2003-09-24	ザプロクターアンドギャンブルカンパニー	ニフッ化酪酸メタロプロテアーゼ阻害物質
WO2001070690A1 (en) *	2000-03-21	2001-09-27	The Procter & Gamble Company	Heterocyclic side chain containing metalloprotease inhibitors
CN1425004A (zh)	2000-03-21	2003-06-18	宝洁公司	含杂环侧链的n－取代的金属蛋白酶抑制剂
GB0011903D0 (en) *	2000-05-18	2000-07-05	Astrazeneca Ab	Combination chemotherapy
JP4975941B2 (ja) *	2000-09-29	2012-07-11	トポターゲットユーケーリミテッド	（ｅ）−ｎ−ヒドロキシ−３−（３−スルファモイル−フェニル）アクリルアミド化合物及びその治療用途
AU2002221099A1 (en) *	2000-12-08	2002-06-18	Takeda Chemical Industries Ltd.	Combination drugs
CZ301712B6 (cs)	2001-01-05	2010-06-02	Pfizer Inc.	Protilátka k receptoru IGF-I a farmaceutický prípravek obsahující tuto protilátku
GB0103303D0 (en)	2001-02-09	2001-03-28	Novartis Ag	Organic compounds
WO2003000194A2 (en)	2001-06-21	2003-01-03	Pfizer Inc.	Thienopyridine and thienopyrimidine anticancer agents
MXPA04004010A (es)	2001-11-01	2004-07-23	Wyeth Corp	Acidos hidroxamicos de aril sulfonamida alenicos como inhibidores de tace y metaloproteinasa de matriz.
AR039067A1 (es)	2001-11-09	2005-02-09	Pfizer Prod Inc	Anticuerpos para cd40
EP1466899A4 (en) *	2001-12-27	2010-01-06	Dainippon Sumitomo Pharma Co	"HYDROXAMIC ACID DERIVATIVE AND MMP INHIBITOR CONTAINING THEM AS AN ACTIVE SUBSTANCE"
WO2003061566A2 (en) *	2002-01-24	2003-07-31	Yissum Research Development Company Of The Hebrew University Of Jerusalem	Anti-cancer combination and use thereof
DE10206404A1 (de) *	2002-02-14	2003-08-28	Gruenenthal Gmbh	Synthese von substituierten Sulfonylaminen
MXPA04008403A (es)	2002-03-01	2004-11-26	Pfizer	Indolil-urea derivados de tienopiridinas utiles como agentes antiangiogenicos, y procedimientos para su uso.
ATE449605T1 (de)	2002-03-13	2009-12-15	Array Biopharma Inc	N3-alkylierte benzimidazol-derivate als mek- hemmer
UA77303C2 (en)	2002-06-14	2006-11-15	Pfizer	Derivatives of thienopyridines substituted by benzocondensed heteroarylamide useful as therapeutic agents, pharmaceutical compositions and methods for their use
AU2003286321A1 (en)	2002-12-19	2004-07-14	Pfizer Inc.	2-(1h-indazol-6-ylamino)-benzamide compounds as protein kinases inhibitors useful for the treatment of ophtalmic diseases
US7199155B2 (en)	2002-12-23	2007-04-03	Wyeth Holdings Corporation	Acetylenic aryl sulfonate hydroxamic acid TACE and matrix metalloproteinase inhibitors
US20060148839A1 (en) *	2003-02-11	2006-07-06	Boehringer Ingelheim International Gmbh	New pharmaceutical compositions based on anticholinergics and tace-inhibitors
PT1603570E (pt)	2003-02-26	2013-03-26	Sugen Inc	Compostos de aminoheteroarilo como inibidores da proteína quinase
HN2004000285A (es)	2003-08-04	2006-04-27	Pfizer Prod Inc	ANTICUERPOS DIRIGIDOS A c-MET
JP2007504122A (ja)	2003-08-29	2007-03-01	ファイザー・インク	新規抗血管形成剤として有用なチエノピリジン−フェニルアセトアミドおよびその誘導体
US7144907B2 (en)	2003-09-03	2006-12-05	Array Biopharma Inc.	Heterocyclic inhibitors of MEK and methods of use thereof
AR045563A1 (es)	2003-09-10	2005-11-02	Warner Lambert Co	Anticuerpos dirigidos a m-csf
JP4768628B2 (ja)	2003-11-19	2011-09-07	アレイバイオファーマ、インコーポレイテッド	Ｍｅｋの二環系阻害剤及びその使用方法
ATE473967T1 (de) *	2003-11-26	2010-07-15	Pfizer Prod Inc	Aminopyrazolderivate als gsk-3-inhibitoren
KR20070036130A (ko)	2004-07-16	2007-04-02	화이자 프로덕츠 인코포레이티드	항-아이지에프-1알 항체를 사용하는 비-혈액학적악성종양에 대한 조합 치료
ITFI20040174A1 (it) *	2004-08-03	2004-11-03	Protera S R L	Derivati arilsolfonammidici dell'acido idrossammico ad azione inibitoria di metalloproteinasi
PT1786785E (pt)	2004-08-26	2010-05-21	Pfizer	Compostos amino-heteroarilo enantiomericamente puros como inibidores da proteína quinase
MY146381A (en)	2004-12-22	2012-08-15	Amgen Inc	Compositions and methods relating relating to anti-igf-1 receptor antibodies
US7429667B2 (en)	2005-01-20	2008-09-30	Ardea Biosciences, Inc.	Phenylamino isothiazole carboxamidines as MEK inhibitors
WO2007044084A2 (en)	2005-05-18	2007-04-19	Array Biopharma Inc.	Heterocyclic inhibitors of mek and methods of use thereof
US8101799B2 (en)	2005-07-21	2012-01-24	Ardea Biosciences	Derivatives of N-(arylamino) sulfonamides as inhibitors of MEK
US7820664B2 (en)	2007-01-19	2010-10-26	Bayer Schering Pharma Ag	Inhibitors of MEK
DK1926996T3 (da)	2005-09-20	2012-01-23	Osi Pharmaceuticals Llc	Biologiske markører, som er prædiktive for anti-cancer-reaktion på insulinlignende vækstfaktor-1-receptorkinasehæmmere
TWI405756B (zh)	2005-12-21	2013-08-21	Array Biopharma Inc	新穎硫酸氫鹽
WO2007117981A2 (en) *	2006-03-29	2007-10-18	Novartis Ag	Selective hydroxamate based mmp inhibitors
WO2007121269A2 (en)	2006-04-11	2007-10-25	Ardea Biosciences, Inc.	N-aryl-n'alkyl sulfamides as mek inhibitors
AU2007237901B2 (en)	2006-04-18	2012-07-05	Ardea Biosciences, Inc.	Pyridone sulfonamides and pyridone sulfamides as MEK inhibitors
EP2121626A1 (en)	2006-12-15	2009-11-25	Pfizer Products Inc.	Benzimidazole derivatives
WO2008129380A1 (en)	2007-04-18	2008-10-30	Pfizer Products Inc.	Sulfonyl amide derivatives for the treatment of abnormal cell growth
US8530463B2 (en)	2007-05-07	2013-09-10	Hale Biopharma Ventures Llc	Multimodal particulate formulations
CL2008001632A1 (es) *	2007-06-05	2009-10-16	Sanofi Aventis	Compuestos derivados de acidos benzoilamino-indan-2-carboxilicos sustituidos, inhibidores del receptor cxcr5; composicion farmaceutica; y su uso en el tratamiento de efecciones fisiologicas inflamatorias, tales como artritis reumatoidea y asma.
CA2924436A1 (en)	2007-07-30	2009-02-05	Ardea Biosciences, Inc.	Pharmaceutical combinations of n-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methoxyphenyl)-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamide as inhibitors of mek and methods of use
JP5421925B2 (ja)	2007-12-19	2014-02-19	ジェネンテック，インコーポレイテッド	５−アニリノイミダゾピリジン及び使用の方法
US8486963B2 (en)	2007-12-21	2013-07-16	Genentech, Inc.	Azaindolizines and methods of use
BRPI0906474A2 (pt)	2008-01-04	2015-07-14	Intellikine Inc	Certas entidades químicas, composições e métodos
US8193182B2 (en)	2008-01-04	2012-06-05	Intellikine, Inc.	Substituted isoquinolin-1(2H)-ones, and methods of use thereof
JP5547099B2 (ja)	2008-03-14	2014-07-09	インテリカイン，エルエルシー	キナーゼ阻害剤および使用方法
CA2756690C (en)	2008-03-28	2016-08-16	Hale Biopharma Ventures, Llc	Administration of benzodiazepine compositions
AU2009268611B2 (en)	2008-07-08	2015-04-09	Intellikine, Llc	Kinase inhibitors and methods of use
EP2334701A4 (en)	2008-10-16	2014-01-08	Univ Pittsburgh	FULLY HUMAN ANTIBODIES AGAINST ANTIGENES ASSOCIATED WITH MELANOMA OF HIGH MOLECULAR WEIGHT AND USES THEREOF
US8476282B2 (en)	2008-11-03	2013-07-02	Intellikine Llc	Benzoxazole kinase inhibitors and methods of use
SG2014009138A (en)	2009-02-05	2014-03-28	Immunogen Inc	Novel benzodiazepine derivatives
WO2010090764A1 (en)	2009-02-09	2010-08-12	Supergen, Inc.	Pyrrolopyrimidinyl axl kinase inhibitors
WO2010099139A2 (en)	2009-02-25	2010-09-02	Osi Pharmaceuticals, Inc.	Combination anti-cancer therapy
US20110171124A1 (en)	2009-02-26	2011-07-14	Osi Pharmaceuticals, Inc.	In situ methods for monitoring the EMT status of tumor cells in vivo
EP2401614A1 (en)	2009-02-27	2012-01-04	OSI Pharmaceuticals, LLC	Methods for the identification of agents that inhibit mesenchymal-like tumor cells or their formation
TW201035088A (en)	2009-02-27	2010-10-01	Supergen Inc	Cyclopentathiophene/cyclohexathiophene DNA methyltransferase inhibitors
EP2401613A2 (en)	2009-02-27	2012-01-04	OSI Pharmaceuticals, LLC	Methods for the identification of agents that inhibit mesenchymal-like tumor cells or their formation
WO2010099138A2 (en)	2009-02-27	2010-09-02	Osi Pharmaceuticals, Inc.	Methods for the identification of agents that inhibit mesenchymal-like tumor cells or their formation
WO2010108652A1 (en)	2009-03-27	2010-09-30	Ardea Biosciences Inc.	Dihydropyridin sulfonamides and dihydropyridin sulfamides as mek inhibitors
WO2010129816A2 (en)	2009-05-07	2010-11-11	Intellikine, Inc.	Heterocyclic compounds and uses thereof
JP2013500991A (ja)	2009-07-31	2013-01-10	オーエスアイ・ファーマシューティカルズ，エルエルシー	ｍＴＯＲ阻害剤および血管新生阻害剤併用療法
PE20170003A1 (es)	2009-08-17	2017-03-15	Intellikine Llc	Compuestos heterociclicos y usos de los mismos
EP2473500A2 (en)	2009-09-01	2012-07-11	Pfizer Inc.	Benzimidazole derivatives
CN102666512B (zh)	2009-10-13	2014-11-26	奥斯特姆医疗公司	对疾病治疗有用的mek抑制剂
WO2011049625A1 (en)	2009-10-20	2011-04-28	Mansour Samadpour	Method for aflatoxin screening of products
PL2496567T3 (pl)	2009-11-05	2018-01-31	Rhizen Pharmaceuticals S A	Nowe benzopiranowe modulatory kinazy
TW201129384A (en)	2010-02-10	2011-09-01	Immunogen Inc	CD20 antibodies and uses thereof
EP3597651A1 (en)	2010-02-12	2020-01-22	Pfizer Inc	Salts and polymorphs of 8-fluoro-2-{4- [(methylamino)methyl]phenyl}-1 ,3,4,5-tetrahydro-6h-azepino[5,4,3- cd]indol-6-one
CA2783665A1 (en)	2010-03-03	2011-09-09	OSI Pharmaceuticals, LLC	Biological markers predictive of anti-cancer response to insulin-like growth factor-1 receptor kinase inhibitors
JP2013527748A (ja)	2010-03-03	2013-07-04	オーエスアイ・ファーマシューティカルズ，エルエルシー	インスリン様増殖因子１受容体キナーゼ阻害剤に対する抗癌反応の予測に役立つ生物学的マーカー
AU2011254242B2 (en)	2010-05-17	2015-10-29	Incozen Therapeutics Pvt. Ltd.	Novel 3,5-disubstitued-3H-imidazo[4,5-b]pyridine and 3,5- disubstitued -3H-[1,2,3]triazolo[4,5-b] pyridine compounds as modulators of protein kinases
JP5951600B2 (ja)	2010-05-21	2016-07-13	インフィニティーファーマシューティカルズ，インコーポレイテッド	キナーゼ調節のための、化合物、組成物および方法
AU2011268356B2 (en)	2010-06-16	2013-09-19	University Of Pittsburgh-Of The Commonwealth System Of Higher Education	Antibodies to endoplasmin and their use
FR2962649A1 (fr)	2010-07-19	2012-01-20	Conservatoire Nat Arts Et Metiers	Traitement d'une pathologie liee a un effet excessif du tnf par un compose de benzene sulfonamide
US9056865B2 (en)	2010-10-20	2015-06-16	Pfizer Inc.	Pyridine-2-derivatives as smoothened receptor modulators
AU2011326427B2 (en)	2010-11-10	2016-01-07	Infinity Pharmaceuticals Inc.	Heterocyclic compounds and uses thereof
CN103648499B (zh)	2011-01-10	2017-02-15	无限药品股份有限公司	用于制备异喹啉酮的方法及异喹啉酮的固体形式
MX2013008833A (es)	2011-02-02	2013-12-06	Amgen Inc	Metodos y composiciones relacionadas con la inhibicion de receptor del factor de crecimiento similar a la insulina 1 (igf-1r).
EP3666289A1 (en)	2011-02-15	2020-06-17	ImmunoGen, Inc.	Cytotoxic benzodiazepine derivatives
WO2012116040A1 (en)	2011-02-22	2012-08-30	OSI Pharmaceuticals, LLC	Biological markers predictive of anti-cancer response to insulin-like growth factor-1 receptor kinase inhibitors in hepatocellular carcinoma
EP2678016B1 (en)	2011-02-23	2016-08-10	Intellikine, LLC	Heterocyclic compounds and uses thereof
WO2012142164A1 (en)	2011-04-12	2012-10-18	The United States Of America, As Represented By The Secretary, Department Of Health & Human Services	Human monoclonal antibodies that bind insulin-like growth factor (igf) i and ii
CA3019531A1 (en)	2011-04-19	2012-10-26	Pfizer Inc.	Combinations of anti-4-1bb antibodies and adcc-inducing antibodies for the treatment of cancer
WO2012149014A1 (en)	2011-04-25	2012-11-01	OSI Pharmaceuticals, LLC	Use of emt gene signatures in cancer drug discovery, diagnostics, and treatment
AP4075A (en)	2011-05-04	2017-03-23	Rhizen Pharmaceuticals S A	Novel compounds as modulators of protein kinases
EP2720699B1 (en)	2011-06-14	2018-05-16	Hale Biopharma Ventures, Llc	Administration of benzodiazepine
WO2013012918A1 (en)	2011-07-19	2013-01-24	Infinity Pharmaceuticals Inc.	Heterocyclic compounds and uses thereof
US8969363B2 (en)	2011-07-19	2015-03-03	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
PL3409278T3 (pl)	2011-07-21	2021-02-22	Sumitomo Pharma Oncology, Inc.	Heterocykliczne inhibitory kinazy białkowej
TW201311663A (zh)	2011-08-29	2013-03-16	Infinity Pharmaceuticals Inc	雜環化合物及其用途
JP5914667B2 (ja)	2011-09-22	2016-05-11	ファイザー・インク	ピロロピリミジンおよびプリン誘導体
US9630979B2 (en)	2011-09-29	2017-04-25	Infinity Pharmaceuticals, Inc.	Inhibitors of monoacylglycerol lipase and methods of their use
US9783613B2 (en)	2011-10-04	2017-10-10	Igem Therapeutics Limited	IgE anti-HMW-MAA antibody
BR112014011115A2 (pt)	2011-11-08	2017-06-13	Pfizer	métodos para tratamento de distúrbios inflamatórios usando anticorpos anti-m-csf
US9452215B2 (en)	2012-02-22	2016-09-27	The Regents Of The University Of Colorado	Bourvadin derivatives and therapeutic uses thereof
EP3345624A1 (en)	2012-02-22	2018-07-11	The Regents Of The University Of Colorado	Bouvardin derivatives and therapeutic uses thereof
JP6192708B2 (ja)	2012-03-30	2017-09-06	ライゼン・ファーマシューティカルズ・エスアー	Ｃ−ｍｅｔプロテインキナーゼ調節物質としての新規３，５−二置換−３ｈ−イミダゾ［４，５−ｂ］ピリジン化合物および３，５−二置換−３ｈ−［１，２，３］トリアゾロ［４，５−ｂ］ピリジン化合物
WO2013152252A1 (en)	2012-04-06	2013-10-10	OSI Pharmaceuticals, LLC	Combination anti-cancer therapy
US8940742B2 (en)	2012-04-10	2015-01-27	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
SI2859017T1 (sl)	2012-06-08	2019-05-31	Sutro Biopharma, Inc.	Protitelesa, ki vsebujejo specifične nenaravne aminokislinske ostanke, postopki njihove priprave in postopki njihove uporabe
DK2863955T3 (en)	2012-06-26	2017-01-23	Sutro Biopharma Inc	MODIFIED FC PROTEINS, INCLUDING LOCATION-SPECIFIC NON-NATURAL AMINO ACID RESIDUES, CONJUGATES THEREOF, METHODS OF PRODUCING ITS AND PROCEDURES FOR USE THEREOF
EP2887965A1 (en)	2012-08-22	2015-07-01	ImmunoGen, Inc.	Cytotoxic benzodiazepine derivatives
US9682934B2 (en)	2012-08-31	2017-06-20	Sutro Biopharma, Inc.	Modified amino acids
EP2909181B1 (en)	2012-10-16	2017-08-09	Tolero Pharmaceuticals, Inc.	Pkm2 modulators and methods for their use
EP2914296B2 (en)	2012-11-01	2021-09-29	Infinity Pharmaceuticals, Inc.	Treatment of cancers using pi3 kinase isoform modulators
US9999680B2 (en)	2013-02-28	2018-06-19	Immunogen, Inc.	Conjugates comprising cell-binding agents and maytansinoids as cytotoxic agents
EP2961435B1 (en)	2013-02-28	2019-05-01	ImmunoGen, Inc.	Conjugates comprising cell-binding agents and cytotoxic agents
MX394360B (es)	2013-03-14	2025-03-24	Sumitomo Pharma Oncology Inc	Inhibidores de jak2 y alk2 y metodos para su uso.
AU2014239542A1 (en)	2013-03-15	2015-10-01	Araxes Pharma Llc	Covalent inhibitors of KRas G12C
WO2014151386A1 (en)	2013-03-15	2014-09-25	Infinity Pharmaceuticals, Inc.	Salts and solid forms of isoquinolinones and composition comprising and methods of using the same
CA2906542A1 (en)	2013-03-15	2014-09-25	Intellikine, Llc	Combination of kinase inhibitors and uses thereof
US9227978B2 (en)	2013-03-15	2016-01-05	Araxes Pharma Llc	Covalent inhibitors of Kras G12C
US9745319B2 (en)	2013-03-15	2017-08-29	Araxes Pharma Llc	Irreversible covalent inhibitors of the GTPase K-Ras G12C
RU2019134551A (ru)	2013-05-30	2019-11-22	Инфинити Фармасьютикалз, Инк.	Лечение злокачественных опухолей с использованием модуляторов изоформ pi3-киназы
WO2014194030A2 (en)	2013-05-31	2014-12-04	Immunogen, Inc.	Conjugates comprising cell-binding agents and cytotoxic agents
WO2015006555A2 (en)	2013-07-10	2015-01-15	Sutro Biopharma, Inc.	Antibodies comprising multiple site-specific non-natural amino acid residues, methods of their preparation and methods of their use
PT3052096T (pt)	2013-10-03	2018-04-04	Kura Oncology Inc	Inibidores de erk e métodos de utilização
EP3964507A1 (en)	2013-10-04	2022-03-09	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
WO2015051241A1 (en)	2013-10-04	2015-04-09	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
JO3805B1 (ar)	2013-10-10	2021-01-31	Araxes Pharma Llc	مثبطات كراس جي12سي
WO2015054572A1 (en)	2013-10-10	2015-04-16	Araxes Pharma Llc	Inhibitors of kras g12c
US9840493B2 (en)	2013-10-11	2017-12-12	Sutro Biopharma, Inc.	Modified amino acids comprising tetrazine functional groups, methods of preparation, and methods of their use
US20160244452A1 (en)	2013-10-21	2016-08-25	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
UA115388C2 (uk)	2013-11-21	2017-10-25	Пфайзер Інк.	2,6-заміщені пуринові похідні та їх застосування в лікуванні проліферативних захворювань
WO2015155624A1 (en)	2014-04-10	2015-10-15	Pfizer Inc.	Dihydropyrrolopyrimidine derivatives
WO2015168079A1 (en)	2014-04-29	2015-11-05	Infinity Pharmaceuticals, Inc.	Pyrimidine or pyridine derivatives useful as pi3k inhibitors
HRP20192056T1 (hr)	2014-04-30	2020-02-21	Pfizer Inc.	Derivati diheterocikla vezani na cikloalkil
ME03334B (me)	2014-06-19	2019-10-20	Ariad Pharma Inc	Heteroarilna jedinjenja za inhibiciju kinaza
WO2016001789A1 (en)	2014-06-30	2016-01-07	Pfizer Inc.	Pyrimidine derivatives as pi3k inhibitors for use in the treatment of cancer
EP3177320B1 (en)	2014-07-31	2021-01-06	The Government of the United States of America as represented by the Secretary of the Department of Health and Human Services	Human monoclonal antibodies against epha4 and their use
JO3556B1 (ar)	2014-09-18	2020-07-05	Araxes Pharma Llc	علاجات مدمجة لمعالجة السرطان
WO2016049524A1 (en)	2014-09-25	2016-03-31	Araxes Pharma Llc	Inhibitors of kras g12c mutant proteins
WO2016049568A1 (en)	2014-09-25	2016-03-31	Araxes Pharma Llc	Methods and compositions for inhibition of ras
EP3233829B1 (en)	2014-12-18	2019-08-14	Pfizer Inc	Pyrimidine and triazine derivatives and their use as axl inhibitors
CA2981530A1 (en)	2015-04-10	2016-10-13	Araxes Pharma Llc	Substituted quinazoline compounds and methods of use thereof
US10428064B2 (en)	2015-04-15	2019-10-01	Araxes Pharma Llc	Fused-tricyclic inhibitors of KRAS and methods of use thereof
CA2982928A1 (en)	2015-04-20	2016-10-27	Tolero Pharmaceuticals, Inc.	Predicting response to alvocidib by mitochondrial profiling
EP3288957A4 (en)	2015-05-01	2019-01-23	Cocrystal Pharma, Inc.	NUCLEOSIDE ANALOGUE FOR THE TREATMENT OF VIRUSES OF THE FLAVIVIIDAE FAMILY AND CANCER
DK3298021T3 (da)	2015-05-18	2019-08-05	Tolero Pharmaceuticals Inc	Alvocidib-prodrugs, der har øget biotilgængelighed
TWI703150B (zh)	2015-06-04	2020-09-01	美商庫拉腫瘤技術股份有限公司	用於抑制ｍｅｎｉｎ及ｍｌｌ蛋白之交互作用的方法及組合物
WO2017009751A1 (en)	2015-07-15	2017-01-19	Pfizer Inc.	Pyrimidine derivatives
US10144724B2 (en)	2015-07-22	2018-12-04	Araxes Pharma Llc	Substituted quinazoline compounds and methods of use thereof
AU2016301315C1 (en)	2015-08-03	2022-07-07	Sumitomo Pharma Oncology, Inc.	Combination therapies for treatment of cancer
HK1261923A1 (zh)	2015-09-14	2020-01-10	Twelve Therapeutics, Inc.	异喹啉酮衍生物的固体形式、其制备方法、包含其的组合物及其使用方法
EP3356354A1 (en)	2015-09-28	2018-08-08	Araxes Pharma LLC	Inhibitors of kras g12c mutant proteins
WO2017058807A1 (en)	2015-09-28	2017-04-06	Araxes Pharma Llc	Inhibitors of kras g12c mutant proteins
EP3356339A1 (en)	2015-09-28	2018-08-08	Araxes Pharma LLC	Inhibitors of kras g12c mutant proteins
WO2017058915A1 (en)	2015-09-28	2017-04-06	Araxes Pharma Llc	Inhibitors of kras g12c mutant proteins
US10647703B2 (en)	2015-09-28	2020-05-12	Araxes Pharma Llc	Inhibitors of KRAS G12C mutant proteins
WO2017058728A1 (en)	2015-09-28	2017-04-06	Araxes Pharma Llc	Inhibitors of kras g12c mutant proteins
US10882847B2 (en)	2015-09-28	2021-01-05	Araxes Pharma Llc	Inhibitors of KRAS G12C mutant proteins
EP3364977A4 (en)	2015-10-19	2019-09-04	Araxes Pharma LLC	PROCESS FOR SCREENING INHIBITORS OF RAS
US10414757B2 (en)	2015-11-16	2019-09-17	Araxes Pharma Llc	2-substituted quinazoline compounds comprising a substituted heterocyclic group and methods of use thereof
MX2018006781A (es)	2015-12-03	2018-11-09	Agios Pharmaceuticals Inc	Inhibidores de mat2a para el tratamiento del cancer que no expresen mtap.
WO2017100546A1 (en)	2015-12-09	2017-06-15	Araxes Pharma Llc	Methods for preparation of quinazoline derivatives
WO2017132615A1 (en)	2016-01-27	2017-08-03	Sutro Biopharma, Inc.	Anti-cd74 antibody conjugates, compositions comprising anti-cd74 antibody conjugates and methods of using anti-cd74 antibody conjugates
EP3199534B1 (en)	2016-02-01	2018-09-05	Galderma Research & Development	Benzenesulfonamide compounds, method for synthesizing same, and use thereof in medicine and cosmetics
CN109152784B (zh)	2016-03-16	2021-12-28	库拉肿瘤学公司	经取代的menin-mll抑制剂及使用方法
MX387806B (es)	2016-03-16	2025-03-19	Kura Oncology Inc	Inhibidores biciclicos con puente sustituidos de menina-mll y metodos de uso
WO2017172979A1 (en)	2016-03-30	2017-10-05	Araxes Pharma Llc	Substituted quinazoline compounds and methods of use
EP3454945B1 (en)	2016-05-12	2022-01-19	The Regents Of The University Of Michigan	Ash1l inhibitors and methods of treatment therewith
US11118233B2 (en)	2016-05-18	2021-09-14	The University Of Chicago	BTK mutation and ibrutinib resistance
US10919914B2 (en)	2016-06-08	2021-02-16	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
US10646488B2 (en)	2016-07-13	2020-05-12	Araxes Pharma Llc	Conjugates of cereblon binding compounds and G12C mutant KRAS, HRAS or NRAS protein modulating compounds and methods of use thereof
CA3035081A1 (en)	2016-09-02	2018-03-08	Dana-Farber Cancer Institute, Inc.	Composition and methods of treating b cell disorders
US10280172B2 (en)	2016-09-29	2019-05-07	Araxes Pharma Llc	Inhibitors of KRAS G12C mutant proteins
CN110312711A (zh)	2016-10-07	2019-10-08	亚瑞克西斯制药公司	作为ras抑制剂的杂环化合物及其使用方法
US11279694B2 (en)	2016-11-18	2022-03-22	Sumitomo Dainippon Pharma Oncology, Inc.	Alvocidib prodrugs and their use as protein kinase inhibitors
WO2018098352A2 (en)	2016-11-22	2018-05-31	Jun Oishi	Targeting kras induced immune checkpoint expression
MX2019007332A (es)	2016-12-19	2019-11-18	Tolero Pharmaceuticals Inc	Péptidos indicadores y métodos para caracterizar sensibilidad.
EP4001269A1 (en)	2016-12-22	2022-05-25	Amgen Inc.	Benzoisothiazole, isothiazolo[3,4-b]pyridine, quinazoline, phthalazine, pyrido[2,3-d]pyridazine and pyrido[2,3-d]pyrimidine derivatives as kras g12c inhibitors for treating lung, pancreatic or colorectal cancer
US20200385364A1 (en)	2017-01-26	2020-12-10	Araxes Pharma Llc	Fused n-heterocyclic compounds and methods of use thereof
EP3573971A1 (en)	2017-01-26	2019-12-04	Araxes Pharma LLC	1-(3-(6-(3-hydroxynaphthalen-1-yl)benzofuran-2-yl)azetidin-1yl)prop-2-en-1-one derivatives and similar compounds as kras g12c modulators for treating cancer
US11274093B2 (en)	2017-01-26	2022-03-15	Araxes Pharma Llc	Fused bicyclic benzoheteroaromatic compounds and methods of use thereof
WO2018140599A1 (en)	2017-01-26	2018-08-02	Araxes Pharma Llc	Benzothiophene and benzothiazole compounds and methods of use thereof
WO2018140514A1 (en)	2017-01-26	2018-08-02	Araxes Pharma Llc	1-(6-(3-hydroxynaphthalen-1-yl)quinazolin-2-yl)azetidin-1-yl)prop-2-en-1-one derivatives and similar compounds as kras g12c inhibitors for the treatment of cancer
CA3051512A1 (en)	2017-01-26	2018-08-02	Zlip Holding Limited	Cd47 antigen binding unit and uses thereof
JP7327802B2 (ja)	2017-01-26	2023-08-16	アラクセスファーマエルエルシー	縮合ヘテロ－ヘテロ二環式化合物およびその使用方法
JP7628392B2 (ja)	2017-03-24	2025-02-10	クラオンコロジー，インク．	血液悪性腫瘍およびユーイング肉腫を処置するための方法
JOP20190272A1 (ar)	2017-05-22	2019-11-21	Amgen Inc	مثبطات kras g12c وطرق لاستخدامها
US10745385B2 (en)	2017-05-25	2020-08-18	Araxes Pharma Llc	Covalent inhibitors of KRAS
US11639346B2 (en)	2017-05-25	2023-05-02	Araxes Pharma Llc	Quinazoline derivatives as modulators of mutant KRAS, HRAS or NRAS
CN110869357A (zh)	2017-05-25	2020-03-06	亚瑞克西斯制药公司	化合物及其用于治疗癌症的使用方法
WO2018226976A1 (en)	2017-06-08	2018-12-13	Kura Oncology, Inc.	Methods and compositions for inhibiting the interaction of menin with mll proteins
US20200207859A1 (en)	2017-07-26	2020-07-02	Sutro Biopharma, Inc.	Methods of using anti-cd74 antibodies and antibody conjugates in treatment of t-cell lymphoma
CN116003405A (zh)	2017-09-08	2023-04-25	美国安进公司	Kras g12c的抑制剂及其使用方法
US11497756B2 (en)	2017-09-12	2022-11-15	Sumitomo Pharma Oncology, Inc.	Treatment regimen for cancers that are insensitive to BCL-2 inhibitors using the MCL-1 inhibitor alvocidib
US12071477B2 (en)	2017-09-18	2024-08-27	Sutro Biopharma, Inc.	Anti-folate receptor alpha antibody conjugated with hemiasterlins
US11649251B2 (en)	2017-09-20	2023-05-16	Kura Oncology, Inc.	Substituted inhibitors of menin-MLL and methods of use
WO2019075367A1 (en)	2017-10-13	2019-04-18	Tolero Pharmaceuticals, Inc.	PKM2 ACTIVATORS IN COMBINATION WITH OXYGEN REACTIVE SPECIES FOR THE TREATMENT OF CANCER
JP2021502388A (ja)	2017-11-10	2021-01-28	ザリージェンツオブザユニバーシティオブミシガン	Ａｓｈ１ｌ阻害剤及びそれを用いた治療方法
CA3084809A1 (en)	2017-12-07	2019-06-13	The Regents Of The University Of Michigan	Nsd family inhibitors and methods of treatment therewith
SG11202009443RA (en)	2018-04-05	2020-10-29	Sumitomo Dainippon Pharma Oncology Inc	Axl kinase inhibitors and use of the same
AU2019262599B2 (en)	2018-05-04	2023-10-12	Amgen Inc.	KRAS G12C inhibitors and methods of using the same
US11090304B2 (en)	2018-05-04	2021-08-17	Amgen Inc.	KRAS G12C inhibitors and methods of using the same
US10988485B2 (en)	2018-05-10	2021-04-27	Amgen Inc.	KRAS G12C inhibitors and methods of using the same
AU2019278998B2 (en)	2018-06-01	2023-11-09	Amgen Inc.	KRAS G12C inhibitors and methods of using the same
EP3813784B1 (en)	2018-06-07	2024-01-10	The Regents Of The University Of Michigan	Prc1 inhibitors and prc1 inhibitors for use in methods of treatment therewith
WO2019241157A1 (en)	2018-06-11	2019-12-19	Amgen Inc.	Kras g12c inhibitors for treating cancer
CA3100390A1 (en)	2018-06-12	2020-03-12	Amgen Inc.	Kras g12c inhibitors encompassing piperazine ring and use thereof in the treatment of cancer
AU2019310590A1 (en)	2018-07-26	2021-01-14	Sumitomo Pharma Oncology, Inc.	Methods for treating diseases associated with abnormal acvr1 expression and acvr1 inhibitors for use in the same
JP2021532157A (ja)	2018-08-01	2021-11-25	アラクセスファーマエルエルシー	がんを処置するための複素環式スピロ化合物およびその使用方法
US20220047716A1 (en)	2018-09-17	2022-02-17	Sutro Biopharma, Inc.	Combination therapies with anti-folate receptor antibody conjugates
JP7628305B2 (ja)	2018-10-24	2025-02-10	アラクセスファーマエルエルシー	腫瘍転移を阻害するためのｇ１２ｃ変異体ｋｒａｓタンパク質の阻害剤としての２－（２－アクリロイル－２，６－ジアザスピロ［３．４］オクタン－６－イル）－６－（１ｈ－インダゾール－４－イル）－ベンゾニトリル誘導体および関連化合物
JP7516029B2 (ja)	2018-11-16	2024-07-16	アムジエン・インコーポレーテツド	Ｋｒａｓｇ１２ｃ阻害剤化合物の重要な中間体の改良合成法
JP7454572B2 (ja)	2018-11-19	2024-03-22	アムジエン・インコーポレーテツド	Ｋｒａｓｇ１２ｃ阻害剤及びその使用方法
JP7377679B2 (ja)	2018-11-19	2023-11-10	アムジエン・インコーポレーテツド	がん治療のためのｋｒａｓｇ１２ｃ阻害剤及び１種以上の薬学的に活性な追加の薬剤を含む併用療法
CN113227092A (zh)	2018-11-29	2021-08-06	亚瑞克西斯制药公司	化合物及其用于治疗癌症的使用方法
MX2021006544A (es)	2018-12-04	2021-07-07	Sumitomo Pharma Oncology Inc	Inhibidores de cinasa dependiente de ciclina 9 (cdk9) y polimorfos de los mismos para uso como agentes para el tratamiento de cancer.
MA54546A (fr)	2018-12-20	2022-03-30	Amgen Inc	Amides d'hétéroaryle utiles en tant qu'inhibiteurs de kif18a
CA3123871A1 (en)	2018-12-20	2020-06-25	Amgen Inc.	Kif18a inhibitors
EP3898592B1 (en)	2018-12-20	2024-10-09	Amgen Inc.	Heteroaryl amides useful as kif18a inhibitors
US20220073504A1 (en)	2018-12-20	2022-03-10	Amgen Inc.	Kif18a inhibitors
WO2020167990A1 (en)	2019-02-12	2020-08-20	Tolero Pharmaceuticals, Inc.	Formulations comprising heterocyclic protein kinase inhibitors
EP3930845A1 (en)	2019-03-01	2022-01-05	Revolution Medicines, Inc.	Bicyclic heterocyclyl compounds and uses thereof
AU2020232242A1 (en)	2019-03-01	2021-09-09	Revolution Medicines, Inc.	Bicyclic heteroaryl compounds and uses thereof
WO2020191326A1 (en)	2019-03-20	2020-09-24	Sumitomo Dainippon Pharma Oncology, Inc.	Treatment of acute myeloid leukemia (aml) with venetoclax failure
JP7547360B2 (ja)	2019-03-22	2024-09-09	スミトモファーマオンコロジー，インコーポレイテッド	Ｐｋｍ２モジュレーターを含む組成物およびそれを使用する処置の方法
WO2020227105A1 (en)	2019-05-03	2020-11-12	Sutro Biopharma, Inc.	Anti-bcma antibody conjugates
EP3738593A1 (en)	2019-05-14	2020-11-18	Amgen, Inc	Dosing of kras inhibitor for treatment of cancers
MX2021014126A (es)	2019-05-21	2022-01-04	Amgen Inc	Formas en estado solido.
CN114302878A (zh)	2019-07-03	2022-04-08	大日本住友制药肿瘤公司	酪氨酸激酶非受体1(tnk1)抑制剂及其用途
AU2020326627A1 (en)	2019-08-02	2022-03-17	Amgen Inc.	KIF18A inhibitors
AU2020324963A1 (en)	2019-08-02	2022-02-24	Amgen Inc.	KIF18A inhibitors
WO2021026100A1 (en)	2019-08-02	2021-02-11	Amgen Inc.	Pyridine derivatives as kif18a inhibitors
AU2020324406A1 (en)	2019-08-02	2022-03-17	Amgen Inc.	KIF18A inhibitors
US20220402916A1 (en)	2019-09-18	2022-12-22	Merck Sharp & Dohme Corp.	Small molecule inhibitors of kras g12c mutant
TW202126636A (zh)	2019-09-30	2021-07-16	美商阿吉歐斯製藥公司	作為ｍｅｎｉｎ抑制劑之六氫吡啶化合物
WO2021081212A1 (en)	2019-10-24	2021-04-29	Amgen Inc.	Pyridopyrimidine derivatives useful as kras g12c and kras g12d inhibitors in the treatment of cancer
JP7340100B2 (ja)	2019-10-28	2023-09-06	メルク・シャープ・アンド・ドーム・エルエルシー	Ｋｒａｓｇ１２ｃ変異型の小分子阻害薬
JP2023515235A (ja)	2019-10-31	2023-04-12	大鵬薬品工業株式会社	４－アミノブタ－２－エンアミド誘導体及びその塩
CR20220241A (es)	2019-11-04	2022-08-03	Revolution Medicines Inc	Inhibidores de ras
CN114901366A (zh)	2019-11-04	2022-08-12	锐新医药公司	Ras抑制剂
CN114867735A (zh)	2019-11-04	2022-08-05	锐新医药公司	Ras抑制剂
BR112022008858A2 (pt)	2019-11-08	2022-09-06	Revolution Medicines Inc	Composto, composição farmacêutica e métodos para inibir sos1 em um sujeito, para inibir a interação de sos1 e uma proteína, para tratar ou prevenir uma doença e para tratar ou prevenir câncer
AR120456A1 (es)	2019-11-14	2022-02-16	Amgen Inc	Síntesis mejorada del compuesto inhibidor de g12c de kras
CN114728960B (zh)	2019-11-14	2025-05-27	美国安进公司	Kras g12c抑制剂化合物的改善的合成
EP4065231A1 (en)	2019-11-27	2022-10-05	Revolution Medicines, Inc.	Covalent ras inhibitors and uses thereof
WO2021106231A1 (en)	2019-11-29	2021-06-03	Taiho Pharmaceutical Co., Ltd.	A compound having inhibitory activity against kras g12d mutation
CA3163703A1 (en)	2020-01-07	2021-07-15	Steve Kelsey	Shp2 inhibitor dosing and methods of treating cancer
WO2021155006A1 (en)	2020-01-31	2021-08-05	Les Laboratoires Servier Sas	Inhibitors of cyclin-dependent kinases and uses thereof
EP4114852A1 (en)	2020-03-03	2023-01-11	Sutro Biopharma, Inc.	Antibodies comprising site-specific glutamine tags, methods of their preparation and methods of their use
WO2021207310A1 (en)	2020-04-08	2021-10-14	Agios Pharmaceuticals, Inc.	Menin inhibitors and methods of use for treating cancer
TW202204333A (zh)	2020-04-08	2022-02-01	美商阿吉歐斯製藥公司	Menin抑制劑及治療癌症之使用方法
US20230174518A1 (en)	2020-04-24	2023-06-08	Taiho Pharmaceutical Co., Ltd.	Kras g12d protein inhibitors
US20230181536A1 (en)	2020-04-24	2023-06-15	Taiho Pharmaceutical Co., Ltd.	Anticancer combination therapy with n-(1-acryloyl-azetidin-3-yl)-2-((1h-indazol-3-yl)amino)methyl)-1h-imidazole-5-carboxamide inhibitor of kras-g12c
AU2021293228A1 (en)	2020-06-18	2023-02-09	Revolution Medicines, Inc.	Methods for delaying, preventing, and treating acquired resistance to RAS inhibitors
AU2021304826A1 (en)	2020-07-10	2023-02-02	The Regents Of The University Of Michigan	GAS41 inhibitors and methods of use thereof
TW202216151A (zh)	2020-07-15	2022-05-01	日商大鵬藥品工業股份有限公司	含有使用於腫瘤之治療之嘧啶化合物之組合
AU2021344830A1 (en)	2020-09-03	2023-04-06	Revolution Medicines, Inc.	Use of SOS1 inhibitors to treat malignancies with SHP2 mutations
US11690915B2 (en)	2020-09-15	2023-07-04	Revolution Medicines, Inc.	Ras inhibitors
TW202237119A (zh)	2020-12-10	2022-10-01	美商住友製藥腫瘤公司	Ａｌｋ﹘５抑制劑和彼之用途
TW202241885A (zh)	2020-12-22	2022-11-01	大陸商上海齊魯銳格醫藥研發有限公司	Ｓｏｓ１抑制劑及其用途
CA3213079A1 (en)	2021-04-13	2022-10-20	Kristin Lynne ANDREWS	Amino-substituted heterocycles for treating cancers with egfr mutations
US11931420B2 (en)	2021-04-30	2024-03-19	Celgene Corporation	Combination therapies using an anti-BCMA antibody drug conjugate (ADC) in combination with a gamma secretase inhibitor (GSI)
CN118234731A (zh)	2021-05-05	2024-06-21	锐新医药公司	Ras抑制剂
CA3217920A1 (en)	2021-05-05	2022-11-10	Andreas BUCKL	Ras inhibitors for the treatment of cancer
JP2024516450A (ja)	2021-05-05	2024-04-15	レボリューションメディシンズインコーポレイテッド	共有結合性ｒａｓ阻害剤及びその使用
EP4347041A1 (en)	2021-05-28	2024-04-10	Taiho Pharmaceutical Co., Ltd.	Small molecule inhibitors of kras mutated proteins
AR127308A1 (es)	2021-10-08	2024-01-10	Revolution Medicines Inc	Inhibidores ras
WO2023056589A1 (en)	2021-10-08	2023-04-13	Servier Pharmaceuticals Llc	Menin inhibitors and methods of use for treating cancer
JP2025500878A (ja)	2021-12-17	2025-01-15	ジェンザイム・コーポレーション	Ｓｈｐ２阻害剤としてのピラゾロピラジン化合物
EP4227307A1 (en)	2022-02-11	2023-08-16	Genzyme Corporation	Pyrazolopyrazine compounds as shp2 inhibitors
WO2023172940A1 (en)	2022-03-08	2023-09-14	Revolution Medicines, Inc.	Methods for treating immune refractory lung cancer
TW202412755A (zh)	2022-04-25	2024-04-01	美商耐斯泰德醫療公司	促分裂原活化蛋白激酶（ｍｅｋ）抑制劑
KR20250022133A (ko)	2022-06-10	2025-02-14	레볼루션 메디슨즈, 인크.	거대고리 ras 억제제
EP4547284A1 (en)	2022-06-30	2025-05-07	Sutro Biopharma, Inc.	Anti-ror1 antibodies and antibody conjugates, compositions comprising anti-ror1 antibodies or antibody conjugates, and methods of making and using anti-ror1 antibodies and antibody conjugates
AR129187A1 (es)	2022-07-08	2024-07-24	Nested Therapeutics Inc	Inhibidores de proteína quinasas activadas por mitógeno (mek)
IL320217A (en)	2022-10-14	2025-06-01	Black Diamond Therapeutics Inc	Methods for treating cancer using isoquinoline or 6-azaquinoline derivatives
TW202504611A (zh)	2023-03-30	2025-02-01	美商銳新醫藥公司	用於誘導ｒａｓｇｔｐ水解之組合物及其用途
WO2024211712A1 (en)	2023-04-07	2024-10-10	Revolution Medicines, Inc.	Condensed macrocyclic compounds as ras inhibitors
AR132338A1 (es)	2023-04-07	2025-06-18	Revolution Medicines Inc	Inhibidores de ras
US20240352036A1 (en)	2023-04-14	2024-10-24	Revolution Medicines, Inc.	Crystalline forms of ras inhibitors, compositions containing the same, and methods of use thereof
WO2024216048A1 (en)	2023-04-14	2024-10-17	Revolution Medicines, Inc.	Crystalline forms of ras inhibitors, compositions containing the same, and methods of use thereof
WO2024226579A1 (en)	2023-04-24	2024-10-31	Nested Therapeutics, Inc.	Heterocyclic derivative as mitogen-activated protein kinase (mek) inhibitor
WO2024229406A1 (en)	2023-05-04	2024-11-07	Revolution Medicines, Inc.	Combination therapy for a ras related disease or disorder
WO2025034702A1 (en)	2023-08-07	2025-02-13	Revolution Medicines, Inc.	Rmc-6291 for use in the treatment of ras protein-related disease or disorder
TW202515582A (zh)	2023-08-24	2025-04-16	日商大塚製藥股份有限公司	西區嘧啶(cedazuridine)之固定劑量組合
US20250154171A1 (en)	2023-10-12	2025-05-15	Revolution Medicines, Inc.	Ras inhibitors
US20250122306A1 (en)	2023-10-13	2025-04-17	Sutro Biopharma, Inc.	Anti-tissue factor antibodies and antibody conjugates, compositions comprising anti-tissue factor antibodies or antibody conjugates, and methods of making and using anti-tissue factor antibodies and antibody conjugates
WO2025085748A1 (en)	2023-10-20	2025-04-24	Merck Sharp & Dohme Llc	Small molecule inhibitors of kras proteins
WO2025090905A1 (en)	2023-10-26	2025-05-01	Nested Therapeutics, Inc.	Crystalline forms of 3-[[3-fluoro-2-(methylsulfamoylamino)-4-pyridyl]methyl]-7-[(3-fluoro-2-pyridyl)oxy]-4-methyl-chromen-2-one
WO2025137507A1 (en)	2023-12-22	2025-06-26	Regor Pharmaceuticals, Inc.	Sos1 inhibitors and uses thereof

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5506242A (en) *	1993-01-06	1996-04-09	Ciba-Geigy Corporation	Arylsufonamido-substituted hydroxamic acids
US5455258A (en) *	1993-01-06	1995-10-03	Ciba-Geigy Corporation	Arylsulfonamido-substituted hydroxamic acids
US5863949A (en)	1995-03-08	1999-01-26	Pfizer Inc	Arylsulfonylamino hydroxamic acid derivatives
WO1998017645A1 (en) *	1996-10-22	1998-04-30	Pharmacia & Upjohn Company	α-AMINO SULFONYL HYDROXAMIC ACIDS AS MATRIX METALLOPROTEINASE INHIBITORS
NZ504387A (en) *	1997-11-12	2002-10-25	Darwin Discovery Ltd	Hydroxamic and carboxylic acid derivatives having MMP and TNF inhibitory activity
IL127496A0 (en) *	1997-12-19	1999-10-28	Pfizer Prod Inc	The use of MMP inhibitors for the treatment of ocular angiogenesis
PA8469501A1 (es) *	1998-04-10	2000-09-29	Pfizer Prod Inc	Hidroxamidas del acido (4-arilsulfonilamino)-tetrahidropiran-4-carboxilico
DE69917124T2 (de) *	1998-04-10	2005-05-12	Pfizer Products Inc., Groton	Cyclobutyl-Aryloxysulfonylamin-Hydroxamsäurederivate

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TNSN98019A1 (fr)	2005-03-15
PE57799A1 (es)	1999-06-11
BG64308B1 (bg)	2004-09-30
EP0977733B1 (en)	2003-09-03
PA8445801A1 (es)	2000-05-24
DE69817801D1 (en)	2003-10-09
PL335027A1 (en)	2000-03-27
TR199901849T2 (xx)	2000-02-21
CN1249743A (zh)	2000-04-05
NO313631B1 (no)	2002-11-04
TW509668B (en)	2002-11-11
DZ2410A1 (fr)	2003-01-04
AR011101A1 (es)	2000-08-02
CO4920234A1 (es)	2000-05-29
AU8191798A (en)	1998-08-25
IL131042A (en)	2004-07-25
JP3765584B2 (ja)	2006-04-12
UA63935C2 (uk)	2004-02-16
DK0977733T3 (da)	2003-11-24
ID22799A (id)	1999-12-09
CA2279276A1 (en)	1998-08-06
UY24866A1 (es)	2000-09-29
IS1950B (is)	2004-10-13
MY121754A (en)	2006-02-28
KR20000070721A (ko)	2000-11-25
CN1113862C (zh)	2003-07-09
IS5129A (is)	1999-07-23
SK101299A3 (en)	2002-04-04
IL131042A0 (en)	2001-01-28
EA199900604A1 (ru)	2000-04-24
KR100317146B1 (ko)	2001-12-22
HN1998000011A (es)	1999-02-09
BR9807815A (pt)	2000-03-08
HRP980058A2 (en)	1998-12-31
ATE248812T1 (de)	2003-09-15
HUP0000852A2 (hu)	2001-05-28
OA11081A (en)	2002-03-14
BG103616A (en)	2000-02-29
ZA98823B (en)	1999-08-02
MA26471A1 (fr)	2004-12-20
JP2000508350A (ja)	2000-07-04
WO1998033768A1 (en)	1998-08-06
SK283963B6 (sk)	2004-06-08
US6303636B1 (en)	2001-10-16
NO993730D0 (no)	1999-08-02
AU721748B2 (en)	2000-07-13
CA2279276C (en)	2005-09-13
NZ336840A (en)	2001-01-26
HRP980058B1 (en)	2002-04-30
PT977733E (pt)	2003-12-31
NO993730L (no)	1999-10-01
GT199800025A (es)	1999-07-24
AP826A (en)	2000-04-28
HK1026203A1 (en)	2000-12-08
DE69817801T2 (de)	2004-03-11
EA002594B1 (ru)	2002-06-27
EP0977733A1 (en)	2000-02-09
AP9801191A0 (en)	1998-03-31

Publication	Publication Date	Title
ES2202796T3 (es)	2004-04-01	Derivados de acidos arilsulfonilaminohidroxamicos.
EP1003720B1 (en)	2004-03-31	Aryloxyarylsulfonylamino hydroxamic acid derivatives
AP733A (en)	1999-02-12	Arylsulfonylamino hydroxamic acid derivatives.
JP3710489B2 (ja)	2005-10-26	アリールスルホニルヒドロキサム酸誘導体
EP0950059B1 (en)	2004-08-04	Cyclic sulfone derivatives
WO1998034915A1 (en)	1998-08-13	N-hydroxy-beta-sulfonyl-propionamide derivatives and their use as inhibitors of matrix metalloproteinases
EP0895988B1 (en)	2002-05-22	Arylsulfonylamino hydroxamic acid derivatives
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